p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside
• CAS No.: 220645-32-9
• Molecular Formula: C₅₉H₆₂O₁₃S
• Molecular Weight: 1011.2
• Mol file: 220645-32-9.mol

Synonyms:p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside

Chemical Property of p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside

There total 6 articles about p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside (220645-28-3) → p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside (220645-32-9)

Guidance literature:

With pyridine hydrogenfluoride; acetic acid; In tetrahydrofuran; for 11h;

DOI:10.1021/ja982232s

Reference yield:

benzoyl chloride (98-88-4) → p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside (220645-32-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / pyridine

2: 58 percent / trifluoroacetic acid / CH₂Cl₂ / 0.33 h / -20 °C

3: 1.) NIS, MS, 2.) TfOH / 1.) CH₂Cl₂, -40 deg C, 20 min, 2.) CH₂Cl₂, from -20 deg C to RT

4: 79 percent / HF*pyridine, AcOH / tetrahydrofuran / 11 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; pyridine hydrogenfluoride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja982232s

Reference yield:

p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside (211801-72-8) → p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside (220645-32-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / aq. NaHCO₃ / tetrahydrofuran; methanol / 6 h / 60 °C

2: 100 percent / pyridine

3: 58 percent / trifluoroacetic acid / CH₂Cl₂ / 0.33 h / -20 °C

4: 1.) NIS, MS, 2.) TfOH / 1.) CH₂Cl₂, -40 deg C, 20 min, 2.) CH₂Cl₂, from -20 deg C to RT

5: 79 percent / HF*pyridine, AcOH / tetrahydrofuran / 11 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja982232s

upstream raw materials:

p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside

benzoyl chloride

p-methylphenyl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-levulinyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

p-methylphenyl 2-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside